Bromopyruvic acid

Chemical compound From Wikipedia, the free encyclopedia

Bromopyruvic acid is the organic compound with the formula BrCH2COCO2H. This colorless solid is the brominated derivative of pyruvic acid. It bears structural similarity to lactic acid and pyruvic acid. It has been investigated as a metabolic poison and an anticancer agent.[1] Like other α-bromoketones, it is a strong alkylating agent.

Quick facts Names, Identifiers ...
Bromopyruvic acid
Skeletal formula of bromopyruvic acid
Ball-and-stick model of the bromopyruvic acid molecule
Names
Preferred IUPAC name
3-Bromo-2-oxopropanoic acid
Other names
Bromopyruvate
3-Bromopyruvic acid
3-Bromopyruvate
3-BrPA
3BP
3-Br-Pyr
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.012.915 Edit this at Wikidata
EC Number
  • 214-206-5
UNII
  • InChI=1S/C3H3BrO3/c4-1-2(5)3(6)7/h1H2,(H,6,7) checkY
    Key: PRRZDZJYSJLDBS-UHFFFAOYSA-N checkY
  • InChI=1/C3H3BrO3/c4-1-2(5)3(6)7/h1H2,(H,6,7)
    Key: PRRZDZJYSJLDBS-UHFFFAOYAU
  • C(C(=O)C(=O)O)Br
  • BrCC(=O)C(=O)O
Properties
C3H3BrO3
Molar mass 166.958 g·mol−1
Appearance white solid
Melting point 79 to 82 °C (174 to 180 °F; 352 to 355 K) (hydrate)
Hazards
GHS labelling:
GHS05: Corrosive
Danger
H290, H314
P260, P264, P280, P301+P330+P331, P303+P361+P353, P304+P340, P305+P351+P338, P310, P321, P363, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Research

Bromopyruvic acid attracts attention in the biomedical research capacity through its potential to inhibit tyrosine phosphatases. Activity of such phosphatases is required for the activation of platelets, especially in a process called venous thromboembolism, a major cause of mortality during gastrointestinal cancer. Bromopyruvic-mediated inhibition of tyrosine phosphatases can counteract such thromboembolism and is investigated as novel angel to combat cancer-associated mortality. [2] The pyruvate transporter system can be used to deliver bromopyruvate inside trypanosomal cells. Once intracellular, the primary target of 3BP is glyceraldehyde-3-phosphate dehydrogenase, which is highly sensitive to inhibition by bromopyruvate.[3] The pyruvate transporter system, which is known to be overexpressed in cancer cells, was later identified to be a monocarboxylate transporter called monocarboxylate transporter 1.[4]

References

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